3-Pyren-1-yl-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester | 697798-09-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 3-Pyren-1-yl-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester
• 英文别名: 1-{[3-(Pyren-1-yl)propanoyl]oxy}pyrrolidine-2,5-dione；(2,5-dioxopyrrolidin-1-yl) 3-pyren-1-ylpropanoate
• CAS: 697798-09-7
• 化学式: C₂₃H₁₇NO₄
• 分子量: 371.392
• InChiKey: YPICDNPPULHDIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  、 3-Pyren-1-yl-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester 在 吡啶 、 4-二甲氨基吡啶 作用下， 以59%的产率得到
  参考文献：
  名称：

  Synthesis, antimicrobial activity, attenuation of aminoglycoside resistance in MRSA, and ribosomal A-site binding of pyrene-neomycin conjugates

  摘要：

  The development of new ligands that have comparable or enhanced therapeutic efficacy relative to current drugs is vital to the health of the global community in the short and long term. One strategy to accomplish this goal is to functionalize sites on current antimicrobials to enhance specificity and affinity while abating resistance mechanisms of infectious organisms. Herein, we report the synthesis of a series of pyreneneomycin B (PYR-NEO) conjugates, their binding affinity to A-site RNA targets, resistance to aminoglycoside-modifying enzymes (AMEs), and antibacterial activity against a wide variety of bacterial strains of clinical relevance. PYR-NEO conjugation significantly alters the affinities of NEO for bacterial A-site targets. The conjugation of PYR to NEO significantly increased the resistance of NEO to AME modification. PYR-NEO conjugates exhibited broad-spectrum activity towards Gram-positive bacteria, including improved activity against NEO-resistant methicillin-resistant Staphylococcus aureus (MRSA) strains. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.11.022
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 3-(1-pyrenyl)propionic acid 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 生成 3-Pyren-1-yl-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester
  参考文献：
  名称：

  Synthesis, antimicrobial activity, attenuation of aminoglycoside resistance in MRSA, and ribosomal A-site binding of pyrene-neomycin conjugates

  摘要：

  The development of new ligands that have comparable or enhanced therapeutic efficacy relative to current drugs is vital to the health of the global community in the short and long term. One strategy to accomplish this goal is to functionalize sites on current antimicrobials to enhance specificity and affinity while abating resistance mechanisms of infectious organisms. Herein, we report the synthesis of a series of pyreneneomycin B (PYR-NEO) conjugates, their binding affinity to A-site RNA targets, resistance to aminoglycoside-modifying enzymes (AMEs), and antibacterial activity against a wide variety of bacterial strains of clinical relevance. PYR-NEO conjugation significantly alters the affinities of NEO for bacterial A-site targets. The conjugation of PYR to NEO significantly increased the resistance of NEO to AME modification. PYR-NEO conjugates exhibited broad-spectrum activity towards Gram-positive bacteria, including improved activity against NEO-resistant methicillin-resistant Staphylococcus aureus (MRSA) strains. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.11.022

文献信息

• Unambiguous Detection of Target DNAs by Excimer−Monomer Switching Molecular Beacons
  作者：Kazuhisa Fujimoto、Hisao Shimizu、Masahiko Inouye

  DOI：10.1021/jo049824f

  日期：2004.5.1

  class of molecular beacons were developed in which pyrene fluorophores were connected both at 3‘ and 5‘ ends of a single-stranded oligonucleotide. The two pyrene-based fluorophores were synthesized from the same starting material, so that the preparation of the beacons was simplified. The detection strategy of the beacons for target DNAs is based on “excimer−monomer emission switching” of the pyrene fluorophores:

  开发了一种新型的分子信标，其中pyr荧光团连接在单链寡核苷酸的3'和5'端。从相同的起始原料合成了两种pyr基荧光团，从而简化了信标的制备。信标针对靶标DNA的检测策略基于the荧光团的“准分子-单体发射转换”：当信标与靶标杂交时，the部分的受激准分子发射变为单体一。这种类型的荧光的两种状态模式可以明确检测目标DNA，因为可以通过荧光变化的等发射点的存在来监视非杂交信标和杂交信标之间严格的1：1相关性。信标可以检测目标19-mer DNA，并可以在1 nM的浓度下将目标与其单核苷酸错配区分开。与传统方法相比，讨论了准分子-单体转换分子信标的优点。
• MASS SPECTROMETRY
  申请人：The Noguchi Institute

  公开号：EP1865312A1

  公开（公告）日：2007-12-12

  An object of the invention is to provide a method for enabling MSn (n>) analysis of a trace amount of a sample and easily and rapidly obtaining structural information by identifying a bonding position of the labeling compound in a molecule with the MSn (n>) analysis. According to the present invention, by labeling a particular moiety of the molecule in a stable manner, ions are easily generated and stabilized, thereby improving sensitivity of the MS. The amount of precursor ions generated in this manner is an amount enough to carry out the MSn (n>1) analysis and to generate structure-specific ions with high reproducibility. The structural information can be easily and rapidly obtained with high sensitivity.

  本发明的目的是提供一种方法，以便能够对痕量样品进行 MSn (n>)分析，并通过 MSn (n>)分析确定标记化合物在分子中的键合位置，从而方便快捷地获得结构信息。根据本发明，通过以稳定的方式标记分子中的特定分子，离子很容易产生和稳定，从而提高 MS 的灵敏度。以这种方式产生的前体离子量足以进行 MSn（n>1）分析，并能以较高的重现性产生结构特异性离子。这样就可以轻松、快速、高灵敏度地获得结构信息。
• A molecular beacon and a method for its synthesis
  申请人：Japan Science and Technology Agency

  公开号：EP2194146B1

  公开（公告）日：2011-12-14
• MALDI MASS ANALYSIS METHOD
  申请人：The Noguchi Institute

  公开号：EP2752659B1

  公开（公告）日：2017-10-18
• Mass Spectrometry
  申请人：Amano Junko

  公开号：US20080138908A1

  公开（公告）日：2008-06-12

  An object of the invention is to provide a method for enabling MS n (n>) analysis of a trace amount of a sample and easily and rapidly obtaining structural information by identifying a bonding position of the labeling compound in a molecule with the MS n (n>) analysis. According to the present invention, by labeling a particular moiety of the molecule in a stable manner, ions are easily generated and stabilized, thereby improving sensitivity of the MS. The amount of precursor ions generated in this manner is an amount enough to carry out the MS n (n>1) analysis and to generate structure-specific ions with high reproducibility. The structural information can be easily and rapidly obtained with high sensitivity.